Go Directly to Jail
by Dani-Ellie03
Summary: Do not pass Go. Do not collect 200. (or, the Charming Family and Captain Swan play Monopoly)


**Title:** Go Directly to Jail  
 **Summary:** Do not pass Go. Do not collect $200. (aka the Charming Family and Captain Swan play Monopoly)  
 **Spoilers:** Up through 4x11, "Heroes and Villains."  
 **Characters:** Emma, Killian, Snow, Charming, and Henry. Charming Family and Captain Swan silliness, here we come!  
 **Rating/Warning:** K+. There is absolutely nothing serious in here, so fluff and silly sweetness all the way!  
 **Disclaimer:** _Once Upon a Time_ and its characters were created by Eddie Kitsis and Adam Horowitz and are owned by ABC. I'm just playing in their toy box.  
 **Author's Note:** Anonymous prompt on Tumblr in response to some previous askbox silliness: "You do realize now that you've gotten going on the Charmings and Monopoly, you have to write it. XD (Well, you obviously don't *have* to do anything, but if you could that would be great!)" And yes, I totally had to, so here we be! Humor still isn't really my strong suit so I hope this comes off as both sweet and sort of funny. Feedback makes my little day! Enjoy. :)

* * *

"No Monopoly," Emma Swan said emphatically.

Killian Jones, who of course had no clue why his Swan would protest the game, arched a questioning eyebrow at her. Snow and David, who had listened to every single one of Emma's arguments against Monopoly many a time, ducked their heads in amusement.

As usual, it was Henry who argued with her. "We _never_ get to play Monopoly," he protested, his tone verging on a whine.

 _Never_ was a bit of an exaggeration. Emma gave in and allowed it sometimes. On very rare occasions when arguing required more energy than she had.

Tonight she just barely had the energy. "And there's a reason for that," she retorted, hoping her somewhat stern tone would end the argument.

The five of them were seated around the kitchen table for one of Snow's re-instituted Game Nights. Game Nights had understandably fallen by the wayside as the family contended with Neverland and New York and the Wicked Witch and the Snow Queen. But now that things had calmed down in Storybrooke in the wake of Gold's banishment, the family had the chance to spend a couple hours playing games after they put baby Neal down for the night … with a new family member of the pirate variety added to the mix.

The board games currently under consideration for this evening's festivities were stacked on the table between them. They'd narrowed the selection down to Sorry, Clue, and Monopoly, despite Emma's vehement insistence that Monopoly be excluded from consideration from now until the end of time.

Unfortunately her kid had other ideas. "I think we should put it to a vote," he said, a mischievous glint making his eyes sparkle. "All in favor of Monopoly, raise your hand."

He eagerly raised his. Snow and David both exchanged an amused glance before lifting their hands into the air, much to Emma's dismay. Killian was about to join them but a glare from Emma kept his hand motionless on the table.

In the end, Killian's solidarity with her didn't matter. "Three against two," Henry spoke up somewhat smugly. "I'll go put Clue and Sorry away."

Emma heaved a sigh and slumped back in her chair, watching Henry ascend the stairs to the loft to tuck the other games back in the armoire in their shared bedroom. "When we all end up frustrated with each other," she said to her parents and Killian, "don't say I didn't warn you."

"I still don't think this is going to go as poorly as you think it is," Snow said gently.

Emma sighed again. "Maybe your experiences with this game are better than mine but I can count the number of times everyone actually had fun throughout an entire Monopoly game on exactly zero hands. It always starts out fine but then once all the properties are sold, everyone gets both bored and frustrated."

Killian raised his eyebrows as he slid the box closer to him in an effort to understand what in the blazes could make his Swan detest this game so. "Aren't these activities supposed to be entertainment? How exactly is this played?"

Emma started to explain the rules but stopped mid-sentence as something hit her. "Oh, great," she said with a groan. "Now we have to figure out how to explain the rules of a board game based on pure capitalism to a pirate."

At least that got them all laughing.

* * *

The first minor argument of the evening occurred during, of all things, the choosing of their tokens. Snow grasped the thimble while David snagged the race car. To the surprise of a grand total of no one, Killian chose the battleship. It was only when Emma reached for the Scottie dog that she found her hand colliding with her son's as he reached for the same piece.

 _Uh_ oh.

Mother and son stared each other down for a beat and then son played dirty. Knowing full well that his mom could never resist his Puppy Dog Eyes, he stuck out his lower lip in the beginnings of a pout.

It was decidedly unfair.

Emma tried to hold out but it was no use. "Ugh, fine," she huffed, reaching for the boot instead. "You can be the dog. One of these days, kid, the Puppy Dog Eyes will stop working for you."

"Maybe," Henry allowed, a triumphant little smirk tugging at his lips, "but that day is obviously not today."

Killian and her parents swallowed chuckles. Emma sent them all a look that plainly told them not to encourage him. "No, I guess it's not."

As Snow got to work distributing everyone's starting wad of colorful cash – she'd apparently become the banker by proxy since no one else volunteered for the job – Emma gave Killian a brief overview of the game. The bewilderment on his face, especially as she got into buying houses and hotels and mortgaging properties for quick cash, struck her as rather amusing. "You think you got all that?" she asked after her little lesson was completed.

"I believe so, love, but I'll volunteer to go last so I can watch the four of you before I take my turn."

It turned out that a pirate picked up rather quickly on the rules of a game based on pure capitalism. He bought everything he landed on, to the point that he owned two railroads by the time he completed his first lap around the board.

Emma, who wasn't having near as much luck, narrowed her eyes at him. How was he doing this?! Up until fifteen minutes ago, he hadn't even known this game existed. "You're going to be a Monopoly shark, aren't you?"

"I don't think you can be a shark if you've never played the game before," David spoke up, hiding a smile.

"Aye, lass, your father speaks the truth," Killian agreed with a shit-eating grin. "However, at its core, this game is about the pursuit of treasure, for which I am remarkably well-suited."

Henry choked on a snicker, and Snow and David were hiding smiles of their own.

Emma just sighed. "You guys won't think it's so funny a few turns from now when he's taking all your money."

* * *

A few turns later, Emma landed on the last unpurchased railroad on the board. Grinning smugly, she handed her mother two hundred dollars. "I'd like to buy the Short Line railroad, please."

"Oi!" Killian, who had the other three railroads, cried. "That was the only one I needed!"

She turned that same smug grin on her pirate, indicating that she knew full well she'd ruined his shot at a railroad monopoly. "You still have all the green properties," she reminded him.

"And the Electric Company," David couldn't help but add.

When Killian had landed on and subsequently purchased the Electric Company, David and Henry had gotten a kick out of it. "Because pirates use oh so much electricity," Henry had chuckled. The kid had also delighted in buying the Water Works before Killian could, both to ruin Killian's chance at a monopoly and because he liked the irony of the pirate not being able to buy the Water Works.

Aside from Killian's green properties, the only other monopoly on the board was Emma's with her yellow properties. She'd also scooped up Boardwalk but Henry had snagged Park Place before she could get her hands on it. Everything else was dispersed pretty evenly among them.

Killian pursed his lips at Emma. "I see now why you protested the playing of this game, love," he sighed as she placed her brand-spanking new title deed for the Short Line railroad in line with her others.

 _Oh, boy_ , Emma thought. "You ain't seen nothin' yet."

And oh, how true that statement was.

An hour later, the game was still raging on. No one seemed to be any closer to hemorrhaging money or quitting but a kind of ennui had begun to set in. Their teasing, which had been coming fast and furious, had begun to drop off as well. "How long does this game typically last, Swan?" a vaguely-bored sounding Killian asked as he watched everyone else take their turns. His battleship currently resided in Jail, where it had been sent by an unlucky drawn from the Chance pile. (He would not hear of paying fifty dollars to get out of Jail early so he was banking on a roll of doubles to pay his bail for him.)

"A million years, seems like," Emma muttered. (No one had landed on any of her yellow properties since she started putting houses on them and she was getting cranky.)

Snow chuckled. "I think our record was what, three and a half hours?"

Killian's eyebrow quirked up in surprise.

"We didn't even finish that game," David added, a smile of amusement playing at his lips. "We decided to pack it up because a couple someones were falling asleep at the table."

"Well, yeah," Emma retorted, unintentionally revealing that she was one of the someones. "We started at eight at night! By eleven-thirty, we were all more than ready for bed."

"I won that game," Henry stage-whispered to Killian.

Killian, who was clearly getting a kick out of their spirited back-and-forth, wrinkled his brow at the kid. "How did you win if you all decided to just stop playing?"

Henry shrugged. "I had the most money when we stopped."

Now the pirate turned his perplexed frown on Emma. " _That's_ how the winner is decided?"

"Not technically," Emma admitted. "The winner is supposed to be the last one standing once everyone else is bankrupt but I can only think of two times in my entire life I've ever actually played this game through to completion. So yeah, we usually just say that the one who has the most money when we decide to throw in the towel is the winner."

He blinked at her.

"Hey, don't look at me," she said as she rolled the dice to take her turn. "I warned all of you that this game is stupid."

Snow, David, and Henry all smiled at each other. Killian smirked at Emma, amusement dancing in his eyes. "Indeed you did, love."

* * *

"Hey, wait," David said as he darted his gaze from his race car to his daughter's boot and back again. "You landed on New York Avenue. You owe me rent!"

"I landed on New York Avenue two turns ago," Emma huffed. "You snooze, you lose."

Killian coughed to cover a snicker.

"I don't believe there is a 'you snooze, you lose' rule in the rule book, Emma," Snow said, her tone equal parts stern and teasing.

Emma rolled her eyes but handed David his sixteen bucks for New York Avenue from two turns ago without another word of complaint. He accepted the cash with a smirk.

Not that the sixteen bucks really mattered to Emma. She'd put more houses on her yellow properties and the rest of the players were finally starting to land on them. She had more money than everyone except Killian.

Once Killian had seen how much money Emma was getting for the houses on her yellow properties, he started building on his green ones. The two of them kept landing on each other's houses as they made their way around the board, essentially trading money back and forth each lap.

"I notice you don't try to shortchange Henry when you land on his properties," Snow teased while giving the kid a surreptitious wink. Henry grinned back.

"That's because the kid pays attention and asks for his money in a timely manner."

"And because you wouldn't stiff your own son," Henry added.

"That, too."

Snow swallowed a laugh.

"But you would stiff your dear old dad?" David asked in mock offense.

"Dear Old Dad should learn to pay attention," Emma replied, hiding a smile.

"It's not like I haven't paid you enough money in rent."

That was the truth. Poor David seemed to land on her Ventnor-with-three-houses more than anyone. "But I always ask for my money in a timely manner, too," she said, smiling sweetly.

Everyone got a good laugh out of that. "Point taken," David chuckled.

* * *

Even though Killian and Emma both kept taking money from Snow, David, and Henry, the three of them managed to survive on pretty much just their money from passing Go and lucky draws of the Chance and Community Chest cards. It had been three hours and there was still no end in sight. No one had even mortgaged any properties!

Emma was fading and she could tell that Henry was, too. Snow and David looked weary. Even Killian, whose enthusiasm for learning the game had carried him thus far, was beginning to tire.

In essence, everyone had had it.

"I think we should call it," Emma said through a yawn.

"I think so, too," Snow agreed.

"Yep." That was Henry.

"Absolutely," David added.

"Aye. Let's tally our treasure." And that was Killian, obviously.

Emma slumped back in her chair in relief. _Finally_.

Everyone counted the money they had left. Snow had a couple hundred and change, David had three sixty-seven, and Henry had seven hundred even. (He'd spent the latter part of the game in Jail for various offenses, which, while boring for him, prevented him from landing on the Killian and Emma monopolies as many times as his grandparents. Emma had of course teasingly bemoaned her kid's descent into a life of perpetual crime.)

Emma dropped the last fake bill onto her pile. "Fifteen ten," she announced.

Killian gave her that shit-eating grin of his. "Sixteen ten."

She gaped at him. "I don't believe you." She swiped his wad of pretend cash and, much to the amusement of everyone else at the table, counted it herself.

Sure enough, there it was, sixteen ten on the nose. Emma narrowed her eyes at Killian. "You beat me by a measly hundred bucks?"

"Pursuit of treasure, remember, love?"

A smiling Emma just shook her head. Pirates.


End file.
